[go: up one dir, main page]

EP0399817B1 - Compositions and process of using in refrigeration - Google Patents

Compositions and process of using in refrigeration Download PDF

Info

Publication number
EP0399817B1
EP0399817B1 EP90305639A EP90305639A EP0399817B1 EP 0399817 B1 EP0399817 B1 EP 0399817B1 EP 90305639 A EP90305639 A EP 90305639A EP 90305639 A EP90305639 A EP 90305639A EP 0399817 B1 EP0399817 B1 EP 0399817B1
Authority
EP
European Patent Office
Prior art keywords
hfc
refrigerant
composition
oil
fluorinated hydrocarbon
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP90305639A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0399817A2 (en
EP0399817A3 (en
Inventor
Thomas Michael Deebs
George Keith Henry
Heather Lee Bergmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0399817A2 publication Critical patent/EP0399817A2/en
Publication of EP0399817A3 publication Critical patent/EP0399817A3/en
Application granted granted Critical
Publication of EP0399817B1 publication Critical patent/EP0399817B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
    • C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/38—Lubricating compositions characterised by the base-material being a macromolecular compound containing halogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only
    • C10M131/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only aliphatic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/24—Only one single fluoro component present
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/0206—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • C10M2211/0225—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
    • C10M2211/0245—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
    • C10M2213/023—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • C10M2213/043—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C10M2213/0606—Perfluoro polymers used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C10M2213/062—Polytetrafluoroethylene [PTFE]
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C10M2213/062—Polytetrafluoroethylene [PTFE]
    • C10M2213/0623—Polytetrafluoroethylene [PTFE] used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/026—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrile group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/32—Wires, ropes or cables lubricants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—Lubricating-sealants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/36—Release agents or mold release agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • This invention relates to lubricants used with refrigerants in compression refrigeration and air-conditioning systems. Specifically, this invention relates to lubricants for use with tetrafluoroethanes, e.g. 1,1,1,2-Tetrafluoroethane (HFC-134a), and 1,1,2,2-Tetrafluoroethane (HFC-134), etc. and of lesser importance, pentafluoroethane (HFC-125). These compounds are being considered as replacements for dichlorodifluoromethane (CFC-12), particularly in automotive air conditioning systems.
  • CFC-12 dichlorodifluoromethane
  • the lubricants of this invention are not only completely miscible over the full operating temperature range for automotive air-conditioning with HFC-134a and the like, but are also completely miscible with CFC-12 over this range. Hence, they may be used with CFC-12 in the same systems during the transition from CFC-12 to HFC-134a.
  • Refrigeration systems that use CFC-12 as the refrigerant generally use mineral oils to lubricate the compressor.
  • CFC-12 is completely miscible with such oils throughout the entire range of refrigeration system temperatures, i.e. -45°C to 65°C.
  • paraffinic and naphthenic oils of about 500 SUS viscosity at 100°F are usually used with CFC-12.
  • These oils have "pour points" below -20°C and viscosities of about 55 SUS at 210°F and are completely miscible with the CFC-12 refrigerant over the range of temperatures from -10°C to 100°C.
  • oil which dissolves in the refrigerant travels through the refrigeration loop in the air conditioning system and returns with the refrigerant to the compressor. It does not separate during condensation, although it may accumulate because of the low temperature when the refrigerant is evaporated. At the same time, this oil which lubricates the compressor will contain some refrigerant which, in turn, may affect its lubricating properties.
  • refrigerants which are not completely miscible with an oil in the full range of mixture compositions and operating temperatures may become miscible or immiscible as the temperature is raised or lowered from room temperature.
  • the areas of immiscibility may assume a variety of shapes, i.e. parabolic or non-parabolic.
  • the curve of miscibility temperature vs. percent oil in the mixture may have its open or concave portion facing the low or high temperatures.
  • the closed or convex-portion of the parabolic curve identifies, respectively, the maximum or minimum temperature above or below which the refrigerant and the lubricating oil are completely miscible. These temperatures are referred to as the maximum or minimum "consolute temperatures.”
  • Beside parabolas these curves can assume skewed parabolic shapes or curves of varying slope wherein immiscibility occurs above or below the curve.
  • One of the objects of this invention is to provide a combination of lubricating oil and refrigerants such as tetrafluoroethane, e.g. HFC-134a, where the area of miscibility encompasses the full range of temperature and composition encountered in compression refrigeration, i.e. complete miscibility occurs for all compositions in the range of -40°C to at least 20°C, preferably to 100°C, the critical temperature of HFC-134a.
  • refrigerants such as tetrafluoroethane, e.g. HFC-134a
  • U.S. Patent No. 4,248,726, issued February 5, 1981, and U.S. Patent No. 4,267,064, issued May 12, 1981, both to Nippon Oil Company et al, relate to the use of a polyglycol oil such as polyoxypropylene glycol (or an alkyl ether thereof) having a viscosity index of at least 150 and a glycidyl ether type epoxy compound as a high viscosity refrigeration oil composition for halogen-containing refrigerants.
  • These polyglycol/glycidyl ether compositions are disclosed for use with Freon® 11, 12, 13, 22, 113, 114, 500 and 502; and as being "particularly effective" with Freon® 12 or 22.
  • U.S. Patent No. 4,755,316 issued July 5, 1988, to Allied-Signal Inc. also relates to the use of polyalkylene glycols.
  • these glycols are at least difunctional with respect to hydroxyl groups and contain at least 80% propylene oxide units relative to the total, the remaining 20% may derive from ethylene or butylene oxide or esters, olefins and the like which are polymerizable with propylene oxide. It should be noted that only 100% oxypropylene units in the difunctional PAGs are exemplified in this patent.
  • DE-A-2221154 describes a lubricating composition for a fluorinated hydrocarbon refrigerant which contains a halogenated aromatic compound, e.g. a halogenated biphenyl or a halogenated diphenyl ether.
  • a halogenated aromatic compound e.g. a halogenated biphenyl or a halogenated diphenyl ether.
  • Patent Abstracts of Japan, C. section, Vol. 13, No. 339, Kokai-no 1-118 598 is an Abstract of Japanese Patent Application 62-277775, According to this Abstract, the Japanese application discloses a lubricating oil for a chlorofluorocarbon refrigerant which is a long chain fluoroalkyl ether.
  • the weight ratio of refrigerant to the lubricant, the " HFC” oil may be anywhere from 99/1 to 1/99, preferably 99/1 to 70/30.
  • the viscosity of these oils may range from 50 to 3000 SUS at 38°C (100°F) but for most commercial uses, from 100 to 1200 SUS at 38°C (100°F).
  • EP additives for use in the invention are included among those disclosed in Table D of US Patent 4,755,316.
  • a preferred one is an organic phosphate; SYN-O-AD (R) 8478, a 70%/30% blend of tri (2,4,6-tri-t-butyl phenyl) phosphate/triphenyl phosphate, manufactured by the Stauffer Chemical Company.
  • EP additives may also be used in conjunction with some of the antiwear additives, oxidation and thermal stability improvers, corrosion inhibitors, viscosity index improvers, detergents and anti-foaming agents disclosed in Table D of US Patent 4,755,316. These additives may also be partially or fully fluorinated.
  • the tetrafluoroethanes e.g. HFC-134a, HFC-134 and the pentafluoroethane HFC-125, particularly HFC-134a have physical characteristics which allow substitution for CFC-12 with only a minimum of equipment changes in compression refrigeration.
  • HFC-134a the preferred tetrafluoroethane refrigerant, may be prepared by any of the methods disclosed in the prior art; e.g. US 2,745,886; 2,887,427; 4,129,603; 4,158,675; 4,311,863; 4,792,643 and British 1,578,933 and 2,030,981.
  • HFC oils may be varied to yield viscosities ranging from 50 to 3000 SUS at 100°F.
  • the monomer(s) may be copolymerized with any of a variety of vinyl compounds including but not limited to vinyl ethers, acrylates, methacrylates, acrylonitrile, vinyl ethoxylates or a halogenated monomer to modify the lubricating properties.
  • the HFC oils may be blended with other lubricants, e.g. perfluorocarbons, to modify viscosity and/or lubrication properties.
  • the lubricants used in the compositions of this invention, and in the invented method for providing lubrication in compression refrigeration and air-conditioning equipment have the following characteristics: Viscosity at 38°C (100°F) 50 to 3000 SUS, preferably 100 to 1200 SUS, particularly about 500 SUS for automotive air-conditioning Pour Point ⁇ -20°C, preferably -20°C to about -50°C and -30°C for the 100 SUS and 500 SUS oils, respectively Solubility or miscibility range 100% from 100°C to (a) less than -40°C for 1-99 weight percent of HFC-134a in mixture with the HFC lubricant of 100°F viscosities of 50 SUS to 2500 SUS (b) less than -30°C for the preferred divinyl ether copolymer, and (c) less than -35°C for the preferred 520 SUS blend.
  • Viscosity at 38°C (100°F) 50 to 3000 SUS preferably 100 to 1200 SUS, particularly about 500 SUS
  • the accuracy of determining the temperatures when the refrigerant/lubricant blend became either miscible or immiscible was about ⁇ 2°C.
  • the refrigerant/lubricant blends were called immiscible when the blend acquired and retained "schlieren" lines: formed floc; or formed two liquid layers. These solubility tests were run from 93° to -50°C. Tests were not run above 93°C for safety reasons. It is assumed that if the blend of HFC-134a/oil is soluble to 93°C, it will still be soluble at100.5°C, the critical temperature of HFC-134a.
  • the tube contents were examined for appearance changes.
  • the refrigerants were then transferred to gas-sampling bulbs for analysis by gas chromatography for the decomposition products of the refrigerant i.e. HFC-143 (the decomposition product of HFC-134a) or HCFC-22 (CFC-12 decomposition product). These results were then converted to their equivalents in terms of HF and HCl generated.
  • the procedure is described fully in ASTM D3233.
  • the V-Block was made of AISI C-1137 steel (HRC-20 to 24 hardness, 12.7 to 25.4 x 10 ⁇ 8m (5 to 10 microinches) surface finish.
  • the test pin was made of AISI 3135 steel (HRB-87 to 91 hardness, 12.7 to 25.4 x 10 ⁇ 8m (5 to 10 microinches) surface finish).
  • 13C - NMR shows several peaks for the product in the range from 123 to 19 ppm, but there is a clear absence of the peaks corresponding to the starting monomer at 126 (triplet) and 123 ppm.
  • the average molecular weight was determined by Vapor phase Osmometry to be 3200.
  • the viscosity and pour point of the product were 1,000 SUS at 100°F and less than -20°C, respectively. Viscosities ranging from 440 to 2540 SUS at 100°F were also made by using process variations. Since the latter oil had a viscosity of 99.6 SUS at 210°F, the viscosity slope (Equation 1) is -4.14. This compares favorably with the slope of -4.23 for a naphthenic oil used with CFC-12 in automotive air-conditioning. This oil's pour point and 40°C and 100°C viscosities are: -23°C, 525 SUS and 55 SUS, respectively.
  • HFC oils were found to be completely miscible with HFC-134a from at least -40° to 93°C, the highest temperature run in the solubility tests.
  • the presence of 1.3 wt. % of SYN-O-AD® 8478 EP additive in the high viscosity oil raised the minimum miscibility temperature from -40° to -35°C.
  • SYN-O-AD® is a product of the Stauffer Chemical Company.
  • CFC-12 is also completely miscible from -40° to 93°C, the HFC oil may be used interchangeably in compressor refrigeration.
  • Table II includes the Suniso® 5GS naphthenic and BVM-100N paraffinic oils currently used with CFC-12 in automotive air-conditioning.
  • the lubricity results with the HFC oil of this example as measured by the "Four-ball wear test” and the "Falex" pin/V-block, load-to-failure test are summarized in Tables III and IV along with other oils.
  • the HFC oil compares very favorably with the naphthenic and paraffinic oils currently used with CFC-12 in automotive air-conditioning.
  • HFC-134a or CFC-12 plus the HFC oil and metals is also superior to the naphthenic and paraffinic oils (Table V).
  • the key to the visual-effect ratings in the table are: 0 - no change, 1 - very very slight, acceptable change, 2 - very slight, borderline change, 3 - slight, but unacceptable change, 4 - moderate, unacceptable change, and 5 - severe change.
  • the range of oil viscosities and the solubilities of these oils in HFC-134a are summarized in Table VI.
  • the acceptable composition range for butyl vinyl ether in the copolymer is about 1 to 30 wt. %, the preferred range is about 1 to 10 wt. %.
  • HFC oils of different viscosities may be blended to adjust for a variety of intermediate viscosities.
  • An HFC oil may also be blended with other oils to obtain a specific viscosity as well, especially if the second oil is also completely soluble in HFC-134a.
  • a specific example of a second oil is: 1,1,1,2,2,3,3,4,4,5,5,6,6 - tridecafluoro-7 hexadecene (TDFH) which has a 38°C (100°F) viscosity of 34 SUS, a pour point of -17°C and is completely miscible in HFC-134a from 93 to -17°C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Lubricants (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP90305639A 1989-05-23 1990-05-23 Compositions and process of using in refrigeration Expired - Lifetime EP0399817B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/356,330 US4944890A (en) 1989-05-23 1989-05-23 Compositions and process of using in refrigeration
US356330 1989-05-23

Publications (3)

Publication Number Publication Date
EP0399817A2 EP0399817A2 (en) 1990-11-28
EP0399817A3 EP0399817A3 (en) 1991-03-27
EP0399817B1 true EP0399817B1 (en) 1993-12-29

Family

ID=23401033

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90305639A Expired - Lifetime EP0399817B1 (en) 1989-05-23 1990-05-23 Compositions and process of using in refrigeration

Country Status (14)

Country Link
US (1) US4944890A (da)
EP (1) EP0399817B1 (da)
JP (1) JP2554387B2 (da)
KR (1) KR900018341A (da)
CN (1) CN1047525A (da)
AT (1) ATE99353T1 (da)
AU (1) AU640652B2 (da)
BR (1) BR9002356A (da)
CA (1) CA2016917A1 (da)
DE (1) DE69005527T2 (da)
DK (1) DK0399817T3 (da)
ES (1) ES2047852T3 (da)
HK (1) HK37594A (da)
ZA (1) ZA903991B (da)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7229567B2 (en) 1997-07-15 2007-06-12 E.I. Dupont De Nemours And Company Refrigerant compositions
US7258813B2 (en) 1999-07-12 2007-08-21 E.I. Du Pont De Nemours And Company Refrigerant composition
US7410595B2 (en) 2002-10-11 2008-08-12 E.I. Du Pont De Nemours And Company Refrigerant compositions
US7641810B2 (en) 2002-11-29 2010-01-05 Neil Andre Roberts Refrigerant compositions

Families Citing this family (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5154846A (en) * 1988-12-27 1992-10-13 Allied-Signal Inc. Fluorinated butylene oxide based refrigerant lubricants
CA2021916A1 (en) * 1989-09-07 1991-03-08 Harry N. Cripps Compositions and process of using in refrigeration
FR2662944B2 (fr) * 1989-11-10 1992-09-04 Atochem Nouveau melange azeotropique a bas point d'ebullition a base de fluoroalcanes et ses applications.
US5108632A (en) * 1990-05-10 1992-04-28 Allied-Signal Inc. Lubricants useful with 1,1-dichloro-2,2,2-trifluoroethane
US5185089A (en) * 1990-05-10 1993-02-09 Allied-Signal Inc. Lubricants useful with 1,1-dichloro-2,2,2-trifluoroethane
US5277834A (en) * 1990-07-26 1994-01-11 E. I. Du Pont De Nemours And Company Near-azeotropic blends for use as refrigerants
WO1992001762A1 (en) 1990-07-26 1992-02-06 E.I. Du Pont De Nemours And Company Near-azeotropic blends for use as refrigerants
US5100569A (en) * 1990-11-30 1992-03-31 Allied-Signal Inc. Polyoxyalkylene glycol refrigeration lubricants having pendant, non-terminal perfluoroalkyl groups
ES2104738T3 (es) * 1991-01-17 1997-10-16 Cpi Eng Services Inc Composicion lubricante para refrigerantes fluorados.
JP2901369B2 (ja) * 1991-01-30 1999-06-07 株式会社日立製作所 冷凍機油組成物とそれを内蔵した冷媒圧縮機及び冷凍装置
WO1992018580A1 (en) * 1991-04-19 1992-10-29 Allied-Signal Inc. Refrigeration compositions of hydrofluorocarbon refrigerant and lubricant
JP2683170B2 (ja) * 1991-07-09 1997-11-26 株式会社ジャパンエナジー 冷凍機油
US5534176A (en) * 1991-07-30 1996-07-09 Alliedsignal Inc. Refrigeration lubricants prepared by polymerizing alkene having a perfluoroalkyl group on one end thereof
DE4139765A1 (de) * 1991-12-03 1993-06-09 Hoechst Ag, 6230 Frankfurt, De Oligomere von fluorierten olefinen
US5399279A (en) * 1991-12-23 1995-03-21 Albemarle Corporation Refrigeration compositions
US5240629A (en) * 1992-01-10 1993-08-31 Ethyl Corporation Refrigerant compositions
US5928557A (en) * 1992-04-09 1999-07-27 Minnesota Mining And Manufacturing Company Lubricants for compressor fluids
CA2137252A1 (en) 1992-06-03 1993-12-09 Nicholas E. Schnur Polyol ester lubricants for refrigerant heat transfer fluids
US5976399A (en) * 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
ATE184310T1 (de) * 1992-06-03 1999-09-15 Henkel Corp Polyol/ester-gemisch als schmiermittel für wärmeträgerflüssigkeiten in kälteanlagen
JP3521216B2 (ja) * 1992-06-03 2004-04-19 コグニス コーポレーション 高温で運転する冷凍コンプレッサー用ポリオールエステル潤滑剤
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
BR9306495A (pt) * 1992-06-04 1998-09-15 Idemitsu Kosan Co Composto de éter polivinílico e um óleo lubrificante
US5518643A (en) * 1992-06-04 1996-05-21 Idemitsu Kosan Co., Ltd. Lubricating oil containing a polyvinyl ether compound for compression-type refrigerators
US5762818A (en) * 1992-07-15 1998-06-09 E. I. Du Pont De Nemours And Company Compositions which include 1,1,2,2- tetrafluoroethane and fluoroethane
US5733472A (en) * 1992-07-15 1998-03-31 E. I. Du Pont De Nemours And Company Compositions which include 1,1,2,2-tetrafluoroethane and fluoropropane
AU5548494A (en) * 1992-11-19 1994-06-08 E.I. Du Pont De Nemours And Company Refrigerant compositions including 1,1,2-trifluoroethane
US5458798A (en) * 1993-02-05 1995-10-17 E. I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of a hydrofluorocarbon and a hydrocarbon
EP0612835B1 (en) * 1993-02-19 1999-08-25 Idemitsu Kosan Company Limited Refrigerating machine oil composition
FR2705140B1 (fr) * 1993-05-11 1995-07-28 Elf Antar France Procédé de remplacement du produit de lubrification pour la conversion des systèmes de réfrigération existant à des fluides frigorigènes sans action sur l'ozone atmosphérique.
MY111325A (en) * 1993-12-03 1999-10-30 Idemitsu Kosan Co A lubricating oil for compression-type refrigerators.
CA2191108C (en) * 1994-05-23 1999-09-28 Nicholas E. Schnur Method for increasing the electrical resistivity of hindered polyol ester refrigerant lubricants
US5910161A (en) * 1994-09-20 1999-06-08 Fujita; Makoto Refrigerating apparatus
TW340870B (en) * 1995-04-07 1998-09-21 Nippon Nogen Co Ltd Lubricating oil additive, lubricating oil and working fluid for refrigerators
JP4112645B2 (ja) * 1996-02-05 2008-07-02 出光興産株式会社 圧縮型冷凍機用潤滑油
GB9624818D0 (en) 1996-11-28 1997-01-15 Rh Ne Poulenc Chemicals Ltd Refrigerant composition
US20010019120A1 (en) 1999-06-09 2001-09-06 Nicolas E. Schnur Method of improving performance of refrigerant systems
US6629419B1 (en) 1999-10-04 2003-10-07 Refringerant Products Ltd. CFC 12 replacement refrigerant
US6604368B1 (en) 1999-10-04 2003-08-12 Refrigerant Products, Ltd. R 12 replacement refrigerant
US6606868B1 (en) 1999-10-04 2003-08-19 Refrigerant Products, Ltd. R 22 replacement refrigerant
GB0206413D0 (en) * 2002-03-19 2002-05-01 Refrigerant Products Ltd Refrigerant for centrifugal compressors
US8444874B2 (en) 2002-10-25 2013-05-21 Honeywell International Inc. Heat transfer methods using heat transfer compositions containing trans-1,3,3,3-tetrafluoropropene
US8033120B2 (en) 2002-10-25 2011-10-11 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US9005467B2 (en) 2003-10-27 2015-04-14 Honeywell International Inc. Methods of replacing heat transfer fluids
DE08020700T1 (de) 2002-10-25 2009-08-13 Honeywell International Inc. Zusammensetzungen mit fluorosubstituierten Olefinen
US9796848B2 (en) 2002-10-25 2017-10-24 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins and methods of foaming
US7279451B2 (en) * 2002-10-25 2007-10-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
US20040089839A1 (en) 2002-10-25 2004-05-13 Honeywell International, Inc. Fluorinated alkene refrigerant compositions
US20090253820A1 (en) * 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
US7655610B2 (en) 2004-04-29 2010-02-02 Honeywell International Inc. Blowing agent compositions comprising fluorinated olefins and carbon dioxide
US20180161076A1 (en) 2003-10-27 2018-06-14 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins, and methods of foaming
US9499729B2 (en) * 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
GB0404343D0 (en) * 2004-02-27 2004-03-31 Rpl Holdings Ltd Refrigerant composition
US8420706B2 (en) * 2005-06-24 2013-04-16 Honeywell International Inc. Foaming agents, foamable compositions, foams and articles containing halogen substituted olefins, and methods of making same
US8574451B2 (en) * 2005-06-24 2013-11-05 Honeywell International Inc. Trans-chloro-3,3,3-trifluoropropene for use in chiller applications
BRPI0707052B8 (pt) * 2006-03-03 2018-05-29 Rpl Holdings Ltd composição refrigerante, e uso de uma composição refrigerante
US8551354B2 (en) * 2006-03-03 2013-10-08 Rpl Holdings Limited Refrigerant composition
US9000061B2 (en) 2006-03-21 2015-04-07 Honeywell International Inc. Foams and articles made from foams containing 1-chloro-3,3,3-trifluoropropene (HFCO-1233zd)
SI3812360T1 (sl) 2009-09-09 2024-02-29 Honeywell International Inc. Monoklorotrifluoropropenske spojine in sestavki ter postopki, ki jih uporabljajo
GB0922288D0 (en) 2009-12-21 2010-02-03 Rpl Holdings Ltd Non ozone depleting and low global warming potential refrigerants for refrigeration
FR2964976B1 (fr) 2010-09-20 2012-08-24 Arkema France Composition a base de 1,3,3,3-tetrafluoropropene
WO2012074121A1 (en) 2010-11-30 2012-06-07 Daikin Industries, Ltd. Hfo refrigerant composition having improved slidability
JPWO2013015201A1 (ja) * 2011-07-22 2015-02-23 旭硝子株式会社 熱サイクル用作動媒体および熱サイクルシステム
US10330364B2 (en) 2014-06-26 2019-06-25 Hudson Technologies, Inc. System and method for retrofitting a refrigeration system from HCFC to HFC refrigerant
CN105779078B (zh) * 2014-12-25 2018-10-16 中国石油天然气股份有限公司 冷冻机油组合物及其制备方法
GB201505230D0 (en) 2015-03-27 2015-05-13 Rpl Holdings Ltd Non ozone depleting and low global warming refrigerant blends
SG11202004304RA (en) 2017-11-27 2020-06-29 Rpl Holdings Ltd Low gwp refrigerant blends
IL302179A (en) 2020-10-22 2023-06-01 Rpl Holdings Ltd Thermal pump refrigerants

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2887427A (en) 1954-08-16 1959-05-19 Worthington Corp Method and apparatus for controlling pulp digesters
US2745886A (en) 1955-01-31 1956-05-15 Dow Chemical Co Process for fluorinating aliphatic halohydrocarbons with a chromium fluoride catalyst and process for preparing the catalyst
AR207202A1 (es) * 1971-05-17 1976-09-22 Thermo King Corp Composicion refrigerante lubricante para un equipo refrigerante a compresor
GB1578933A (en) 1977-05-24 1980-11-12 Ici Ltd Manufacture of halogenated hydrocarbons
US4158675A (en) 1977-09-23 1979-06-19 Imperial Chemical Industries Limited Manufacture of halogenated compounds
US4129603A (en) 1978-02-07 1978-12-12 Imperial Chemical Industries Limited Manufacture of halogenated compounds
JPS5527139A (en) 1978-08-14 1980-02-27 Daikin Ind Ltd Preparation of tetrafluoroethane
US4359394A (en) * 1978-10-30 1982-11-16 Thermo King Corporation Thermally stable lubricants for refrigerator systems
US4311863A (en) 1980-06-11 1982-01-19 E. I. Du Pont De Nemours & Company Process for the manufacture of 1,1,1,2-tetrafluoroethane
JPS5988166A (ja) 1982-11-10 1984-05-22 ダイキン工業株式会社 消火剤
JPS6096684A (ja) * 1983-11-01 1985-05-30 Asahi Glass Co Ltd 耐熱性が向上した作動媒体組成物
DE3415975A1 (de) 1984-04-28 1985-10-31 Hoechst Ag, 6230 Frankfurt Fluorhaltige copolymerisate, verfahren zu ihrer herstellung und ihre verwendung
KR900003913B1 (ko) 1984-11-22 1990-06-04 다이낑고오교가부시끼가이샤 퍼플루오로 알킬비닐중합체의 제조방법
US4758366A (en) * 1985-02-25 1988-07-19 Widger Chemical Corporation Polyhalogenated hydrocarbon refrigerants and refrigerant oils colored with fluorescent dyes and method for their use as leak detectors
JP2617449B2 (ja) 1986-05-26 1997-06-04 日本電気株式会社 半導体受光素子
US4792643A (en) 1987-06-16 1988-12-20 Kaiser Aluminum & Chemical Corporation Catalyst and process for 1,1,1,2-tetrafluoroethane by vapor phase reaction
US4755316A (en) 1987-10-23 1988-07-05 Allied-Signal Inc. Refrigeration lubricants
JPH0625340B2 (ja) * 1988-03-07 1994-04-06 株式会社日立製作所 作動媒体及びその用途
US5032306A (en) * 1989-09-07 1991-07-16 E. I. Du Pont De Nemours And Company Fluorinated hydrocarbon lubricants for use with refrigerants in compression refrigeration

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7229567B2 (en) 1997-07-15 2007-06-12 E.I. Dupont De Nemours And Company Refrigerant compositions
US7258813B2 (en) 1999-07-12 2007-08-21 E.I. Du Pont De Nemours And Company Refrigerant composition
US7410595B2 (en) 2002-10-11 2008-08-12 E.I. Du Pont De Nemours And Company Refrigerant compositions
US7648642B2 (en) 2002-10-11 2010-01-19 E.I. Du Pont De Nemours And Company Refrigerant compositions
US7799240B1 (en) 2002-10-11 2010-09-21 E.I. Du Pont De Nemours And Company Refrigerant compositions
US7837894B2 (en) 2002-10-11 2010-11-23 E. I. Du Pont De Nemours And Company Refrigerant compositions
US7641810B2 (en) 2002-11-29 2010-01-05 Neil Andre Roberts Refrigerant compositions
US7713434B2 (en) 2002-11-29 2010-05-11 E.I. Du Pont De Nemours And Company Refrigerant compositions
US7771610B2 (en) 2002-11-29 2010-08-10 E.I. Du Pont De Nemours And Company Refrigerant compositions
US8246851B2 (en) 2002-11-29 2012-08-21 Roberts Neil Andre Chiller refrigerants

Also Published As

Publication number Publication date
JP2554387B2 (ja) 1996-11-13
DE69005527T2 (de) 1994-06-16
ES2047852T3 (es) 1994-03-01
CA2016917A1 (en) 1990-11-23
DE69005527D1 (de) 1994-02-10
BR9002356A (pt) 1991-08-06
US4944890A (en) 1990-07-31
JPH039995A (ja) 1991-01-17
ATE99353T1 (de) 1994-01-15
ZA903991B (en) 1992-01-29
AU5576390A (en) 1990-11-29
DK0399817T3 (da) 1994-01-24
KR900018341A (ko) 1990-12-21
AU640652B2 (en) 1993-09-02
CN1047525A (zh) 1990-12-05
EP0399817A2 (en) 1990-11-28
HK37594A (en) 1994-04-29
EP0399817A3 (en) 1991-03-27

Similar Documents

Publication Publication Date Title
EP0399817B1 (en) Compositions and process of using in refrigeration
EP0402009B1 (en) Compositions for compression refrigeration and method of using them
US5053155A (en) Compositions and process for use in refrigeration
US5032306A (en) Fluorinated hydrocarbon lubricants for use with refrigerants in compression refrigeration
EP0428757B1 (en) Lubricating oil composition
US5154846A (en) Fluorinated butylene oxide based refrigerant lubricants
US5384057A (en) Compositions and process of using in refrigeration
EP0400894B1 (en) Refrigeration compositions and process for using
US5145594A (en) Cyanocarbon compounds as lubricants in refrigeration compositions
US5017300A (en) Compositions and process for use in refrigeration
WO1992009670A1 (en) Polyoxyalkylene glycol refrigeration lubricants having a partially fluorinated polymer backbone
US5037570A (en) Refrigeration compositions and process for using
US5928557A (en) Lubricants for compressor fluids
US4931199A (en) Use of chlorofluoropolyethers as lubricants for refrigerants
JP2771539B2 (ja) フロン冷媒用潤滑油
US5378385A (en) Partially fluorinated silicone refrigeration lubricants
US5198139A (en) Use of chlorofluoropolymers as lubricants for refrigerants
US5286398A (en) End-capped polyalkylene oxide compositions with hydroxyl group functionality and use thereof for lubrication in refrigeration systems
EP0421586A1 (en) Compositions and process of using in refrigeration
US5534176A (en) Refrigeration lubricants prepared by polymerizing alkene having a perfluoroalkyl group on one end thereof
WO1993006196A1 (en) Compositions and process for use in refrigeration
CA2048909C (en) Refrigerant lubricant compositions
JP2580448B2 (ja) フロン圧縮機用潤滑油、該澗滑油とフロン冷媒とを混合したフロン圧縮機用組成物及び前記潤滑油を用いたフロン圧縮機の潤滑方法
GB2149814A (en) Pumping heat using lubricated compressor
JPH02173195A (ja) フロン圧縮機用潤滑油

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

17P Request for examination filed

Effective date: 19901217

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

17Q First examination report despatched

Effective date: 19921113

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

REF Corresponds to:

Ref document number: 99353

Country of ref document: AT

Date of ref document: 19940115

Kind code of ref document: T

REG Reference to a national code

Ref country code: DK

Ref legal event code: T3

ITF It: translation for a ep patent filed
REF Corresponds to:

Ref document number: 69005527

Country of ref document: DE

Date of ref document: 19940210

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2047852

Country of ref document: ES

Kind code of ref document: T3

ET Fr: translation filed
REG Reference to a national code

Ref country code: GR

Ref legal event code: FG4A

Free format text: 3010800

EPTA Lu: last paid annual fee
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
EAL Se: european patent in force in sweden

Ref document number: 90305639.8

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20090504

Year of fee payment: 20

Ref country code: ES

Payment date: 20090605

Year of fee payment: 20

Ref country code: DK

Payment date: 20090514

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20090527

Year of fee payment: 20

Ref country code: SE

Payment date: 20090512

Year of fee payment: 20

Ref country code: LU

Payment date: 20090616

Year of fee payment: 20

Ref country code: IT

Payment date: 20090522

Year of fee payment: 20

Ref country code: FR

Payment date: 20090515

Year of fee payment: 20

Ref country code: AT

Payment date: 20090514

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 20090428

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20090513

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GR

Payment date: 20090421

Year of fee payment: 20

Ref country code: GB

Payment date: 20090520

Year of fee payment: 20

REG Reference to a national code

Ref country code: NL

Ref legal event code: V4

Effective date: 20100523

BE20 Be: patent expired

Owner name: E.I. *DU PONT DE NEMOURS AND CY

Effective date: 20100523

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: DK

Ref legal event code: EUP

EUG Se: european patent has lapsed
REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20100524

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20100523

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20100524

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20100522

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20100523